Acetaldehyde → 6-[1-[3-(Ethylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid methyl ester

HRID 381346Notes

Reaction equation

HRID 381346 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])=[N:6][CH:5]=1.[CH:26](=O)[CH3:27].[Na].C([BH3-])#N.[Na+].[OH-].[Na+]>O.C(O)(=O)C.CO>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:23]([NH:24][CH2:26][CH3:27])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])=[N:6][CH:5]=1

Participants

9

Reactant 5

HCID 177AcetaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 5360545SodiumHCID 206964266-[1-(3-Amino-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid methyl ester

Product 1

HCID 702122536-[1-[3-(Ethylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid methyl esterYield 76%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6-[1-(3-amino-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid methyl ester (5 g) was added to methanol (100 ml) and with the addition of acetic acid (4 ml) and acetaldehyde (1.2 ml) at 5° C.˜10° C., the mixture was stirred for 30 minutes. With the addition of sodium cyanoborohyride (1 g), the mixture was stirred at 15° C. for 2 hours. Sodium cyanoborohydride (1 g) was added again, and the mixture was further stirred for 1 hour. Water (50 ml) and 3N-sodium hydroxide solution were added to the mixture for neutralization (pH 7.5) and then, methanol was concentrated under reduced pressure. After the mixture was extracted with chloroform, the separated organic layer was concentrated under reduced pressure. The residue was treated with ether for crystallization and recrystallized with ethyl acetate and hexane. The product was filtered and dried to give a desired compound of 4.1 g (yield: 76%).

Workup

  1. stirringthe mixture was stirred at 15° C. for 2 hours
  2. stirringthe mixture was further stirred for 1 hour
  3. concentrationmethanol was concentrated under reduced pressure
  4. extractionAfter the mixture was extracted with chloroform
  5. concentrationthe separated organic layer was concentrated under reduced pressure
  6. additionThe residue was treated with ether for crystallization
  7. customrecrystallized with ethyl acetate and hexane
  8. filtrationThe product was filtered
  9. customdried

Sources & evidence

ORD record
ord-9712a97442cf4ff68f6738ea1c850717
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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